Stadium: Palasport Round: 45 Ground: Hardcourt indoor
| Challenger Istanbul | 2018/09/10 07:30 | Tim Van Rijthoven v Tobias Simon | 6-3,7-6 |
| Challenger Istanbul | 2018/09/09 09:00 | Vladimir Polyakov v Tobias Simon | 0-6,3-6 |
| Challenger Istanbul | 2018/09/08 07:00 | Isaac Stoute v Tobias Simon | 3-6,6-4,4-6 |
| Challenger Mallorca | 2018/08/28 09:30 | Tobias Simon v Sergio Gutierrez-Ferrol | 6-3,6-2 |
| Challenger Mallorca | 2018/08/27 11:10 | Tobias Simon v Hugo Grenier | 7-5,2-6,7-6 |
| Challenger Mallorca | 2018/08/26 15:45 | Tobias Simon v Federico Zeballos | 7-6,7-6 |
| Challenger Mallorca | 2018/08/26 10:45 | Yannick Mertens v Tobias Simon | 7-6,4-6,4-6 |
| Challenger Pullach Qual | 2018/08/04 15:25 | Zizou Bergs v Tobias Simon | 6-4,7-6 |
| Challenger Barletta Qual | 2018/04/07 14:25 | Savino Lapalombella v Maxime Chazal | 0-6,1-6 |
| Challenger Andria Qual | 2017/11/18 09:00 | Savino Lapalombella v Giuseppe Tresca | 0-6,1-6 |
| Challenger Barletta Qual | 2017/04/08 12:10 | Savino Lapalombella v Giorgio Portaluri | 1-6,1-6 |
| Challenger Andria Qual | 2016/11/19 13:10 | Savino Lapalombella v Riccardo Bonadio | 0-6,1-6 |
| Challenger Barletta Qual | 2016/04/09 10:35 | Savino Lapalombella v Lorenzo Sonego | 0-6,1-6 |